Master of Science (MSc)
Faculty of Science
Dr. Kenneth Maly
The overall theme of this research was to synthesize and study the structure-property relationships of novel polycyclic aromatic compounds capable of self-assembling to form liquid crystalline, and microporous structures, as well as molecules capable of molecular recognition. The unifying theme that connects this research is the utilization of the Yamamoto coupling reaction to access the desired polycyclic aromatic hydrocarbon targets. More specifically, the scope of the Yamamoto coupling reaction was explored for the synthesis of electron-deficient triphenylene derivatives that are otherwise difficult to prepare. The molecules prepared via the Yamamoto coupling reaction are expected to be further utilized as intermediates for the synthesis of novel target materials. This thesis had three main goals. The first goal was the synthesis of electron-deficient triphenylene 1 via the Yamamoto coupling reaction followed by the study of the influences of thionation on the liquid crystalline and electron properties through the synthesis of 2. In the second goal, we sought to prepare electron-deficient triphenylene 3 via the Yamamoto coupling reaction and use as a building block towards the preparation of a covalent organic framework 4. Finally, we investigated a novel route to access an extended tetraphenylene derivative 5. Thus far, targets 1 and 2 have been prepared in 65% and 60% yield, respectively and the affects of thionation on the mesomorphic and electronic properties of 1 were investigated. Moreover, progress towards the synthesis of triphenylene 3 has been made, however, purification of 3 has proven to be difficult under the current conditions. Finally, important intermediates have been accessed in good yields towards compound 5, and its construction remains in progress.
LeDrew, Josh, "Utilization of the Yamamoto Cyclotrimerization Reaction Towards the Synthesis of Polycyclic Aromatic Compounds" (2022). Theses and Dissertations (Comprehensive). 2433.
Available for download on Saturday, December 23, 2023